2-Nitroaniline → HCID 10730528, compound

HRID 395736Notes

Reaction equation

HRID 395736 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[N:2].C(N(CC)CC)C.[N+:19]([C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24])([O-:21])=[O:20]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:24][C:23]1[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=1[N+:19]([O-:21])=[O:20])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 69462-NitroanilineHCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 10730528HCID 10730528, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-cyanobenzoyl chloride (10.0 g, 60.4 mmol), triethylamine (12.6 mL, 90.6 mmol), and methylene chloride (120 mL) was added 2-nitroaniline (8.30 g, 60.4 mmol) followed by 4-(dimethylamino)pyridine (738 mg, 6.04 mmol). After stirring for 24 h, the reaction mixture was concentrated in vacuo. Chromatography (silica gel, 30% ethyl acetate/70% hexanes to 50% ethyl acetate/50% hexanes) yielded 17.1 g (99%) of the title compound as a yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ffc25edb05e9468b834371db060d155f
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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